Bovine Metabolome Database: Showing metabocard for 3-Methylhistidine (BMDB0000479)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:20 UTC

Update Date

2020-06-04 20:20:16 UTC

BMDB ID

BMDB0000479

Secondary Accession Numbers

BMDB00479

Metabolite Identification

Common Name

3-Methylhistidine

Description

N(pros)-Methyl-L-histidine, also known as 3-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N(pros)-Methyl-L-histidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N(pros)-Methyl-L-histidine exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid	ChEBI
3-Methyl-L-histidine	ChEBI
N-pros-Methyl-L-histidine	ChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoate	Generator
3-N-Methyl-L-histidine	HMDB
L-3-Methylhistidine	HMDB
N(pros)-Methyl-L-histidine	HMDB
N3-Methyl-L-histidine	HMDB
3-Methylhistidine hydride	HMDB
3-Methylhistidine dihydrochloride	HMDB
3-Methylhistidine	ChEBI
Pi methylhistidine	HMDB
N(Pi)-methylhistidine	HMDB
N Pi-methylhistidine	HMDB

Chemical Formula

C₇H₁₁N₃O₂

Average Molecular Weight

169.1811

Monoisotopic Molecular Weight

169.085126611

IUPAC Name

(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

Traditional Name

3,methylhistidine

CAS Registry Number

368-16-1

SMILES

[H][C@](N)(CC1=CN=CN1C)C(O)=O

InChI Identifier

InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1

InChI Key

JDHILDINMRGULE-LURJTMIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:27596 )
L-histidine derivative (CHEBI:27596 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	200 mg/mL at 25 °C	BEILSTEIN
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.96 m³·mol⁻¹	ChemAxon
Polarizability	16.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-ab7d6324146b8775fe50	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-42443c78fdfca9db1926	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0900000000-e6ce7548fd6f09e2098f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-2900000000-77f55ec21b9e637c0148	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-25e42ab3c1bd0832a7fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-3900000000-fb4a45b41e8cb903c156	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-0a98679ff9db2f56925a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-7b29b213a49dfa3c0f7d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0900000000-5a4990ec47e6292c0f7f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-993e2b71358969de5168	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9500000000-1817d9d8adbfaf0595f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9100000000-2e05be86f146c22455ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-2900000000-15f0e43eb0d06e7f3ef3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9200000000-5a1ab4d052e6ba4a76e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0002-9000000000-c1951c88c84885804fb6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-4e0fea0fe9b1142db07b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0592-4900000000-ee1bce969d650e9fcfbe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0002-9000000000-a87ff5cc0642ea3af69c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0002-9000000000-28a73708493f968c2ac6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9800000000-6565ccf96757ef3bc08f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-2d351351f285b2188710	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0592-4900000000-ee1bce969d650e9fcfbe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-2ed34e7b458d9f8c092f	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Liver
Longissimus Thoracis Muscle
Milk
Placenta
Prostate Tissue
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
beta-Alanine Metabolism		Not Available
Histidine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	14 +/- 2 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24440255	details
Liver	Detected and Quantified	25 +/- 5 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	35 +/- 8 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	103 - 151 uM	Not Specified	Not Specified	Normal	PMID: 20338431	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	2 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	35 +/- 9 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	19 +/- 4 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000479

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093613

KNApSAcK ID

Not Available

Chemspider ID

58494

KEGG Compound ID

C01152

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Methylhistidine

METLIN ID

5466

PubChem Compound

64969

PDB ID

Not Available

ChEBI ID

27596

References

Synthesis Reference

Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details

1. Protein arginine N-methyltransferase 6

General function:: Involved in histone binding
Specific function:: Arginine methyltransferase that can catalyze the formation of both omega-N monomethylarginine (MMA) and asymmetrical dimethylarginine (aDMA), with a strong preference for the formation of aDMA. Preferentially methylates arginyl residues present in a glycine and arginine-rich domain and displays preference for monomethylated substrates. Specifically mediates the asymmetric dimethylation of histone H3 'Arg-2' to form H3R2me2a. H3R2me2a represents a specific tag for epigenetic transcriptional repression and is mutually exclusive with methylation on histone H3 'Lys-4' (H3K4me2 and H3K4me3). Acts as a transcriptional repressor of various genes such as HOXA2, THBS1 and TP53 (By similarity). Repression of TP53 blocks cellular senescence (By similarity). Also methylates histone H2A and H4 'Arg-3' (H2AR3me and H4R3me, respectively). Acts as a regulator of DNA base excision during DNA repair by mediating the methylation of DNA polymerase beta (POLB), leading to the stimulation of its polymerase activity by enhancing DNA binding and processivity. Methylates HMGA1. Regulates alternative splicing events. Acts as a transcriptional coactivator of a number of steroid hormone receptors including ESR1, ESR2, PGR and NR3C1. Promotes fasting-induced transcriptional activation of the gluconeogenic program through methylation of the CRTC2 transcription coactivator. Methylates GPS2, protecting GPS2 from ubiquitination and degradation. Methylates SIRT7, inhibiting SIRT7 histone deacetylase activity and promoting mitochondria biogenesis (By similarity).
Gene Name:: PRMT6
Uniprot ID:: Q5E9L5
Molecular weight:: 41868.0

Reactions

L-Histidine + S-Adenosylmethionine → 3-Methylhistidine + S-Adenosylhomocysteine	details

Enzyme Details

2. Cytosolic non-specific dipeptidase

General function:: Amino acid transport and metabolism
Specific function:: Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly. Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis.
Gene Name:: CNDP2
Uniprot ID:: Q3ZC84
Molecular weight:: 52655.0

Reactions

Anserine + Water → Beta-Alanine + 3-Methylhistidine	details

Showing metabocard for 3-Methylhistidine (BMDB0000479)

Structure for BMDB0000479 (3-Methylhistidine)

Enzymes

Reactions

Reactions